methyl 2-(2,6-dimethylanilino)propanoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 990.3 g (= 4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methyl ester is mixed with 605 g (= 5.7 g-moles) of sodium carbonate in 2.5 liters of benzene (absolute). An amount of 455 ml (= 5.7 g-moles) of monochloroacetyl chloride is then added dropwise and sufficiently slowly to ensure that a temperature of 30°-35° in the reaction mixture is not exceeded. After stirring has been maintained overnight at room temperature, the mixture is filtered off, and the filtrate concentrated in a rotary evaporator at ca. 50°. The resulting residue is recrystallised from ligroin (boiling range 65°-90° ). The yield obtained is 1132 g (= 83.8% of theory) of final product, M.P. 92°-94° (compound No. 3). to ensure that a temperature of 30°-35° in the reaction mixture the mixture is filtered off the filtrate concentrated in a rotary evaporator at ca. 50° The resulting residue is recrystallised from ligroin (boiling range 65°-90° ) The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 990.3 g (= 4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methyl ester is mixed with 605 g (= 5.7 g-moles) of sodium carbonate in 2.5 liters of benzene (absolute). An amount of 455 ml (= 5.7 g-moles) of monochloroacetyl chloride is then added dropwise and sufficiently slowly to ensure that a temperature of 30°-35° in the reaction mixture is not exceeded. After stirring has been maintained overnight at room temperature, the mixture is filtered off, and the filtrate concentrated in a rotary evaporator at ca. 50°. The resulting residue is recrystallised from ligroin (boiling range 65°-90° ). The yield obtained is 1132 g (= 83.8% of theory) of final product, M.P. 92°-94° (compound No. 3). to ensure that a temperature of 30°-35° in the reaction mixture the mixture is filtered off the filtrate concentrated in a rotary evaporator at ca. 50° The resulting residue is recrystallised from ligroin (boiling range 65°-90° ) The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g-moles of 2,6-dimethylaniline, 6.6 g-moles of NaHCO3 and 18.0 g-moles of α-bromopropionic acid methyl ester are placed together and heated slowly, with stirring, for 1 hour upto 120°-125° C. bath temperature. As CO2 is evolved, stirring of the mixture at this temperature is continued for 18 hours. The mixture is subsequently cooled, the inorganic constituents are filtered off, and the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr). After removal of the excess α-bromopropionic acid methyl ester, the resulting yield is 990.3 g (79.6% of theory) of final product, which boils at 133°-134° (12 Torr). heated slowly stirring of the mixture at this temperature is continued for 18 hours The mixture is subsequently cooled the inorganic constituents are filtered off the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr) After removal of the excess α-bromopropionic acid methyl ester

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g-moles of 2,6-dimethylaniline, 6.6 g-moles of NaHCO3 and 18.0 g-moles of α-bromopropionic acid methyl ester are placed together and heated slowly, with stirring, for 1 hour upto 120°-125° C. bath temperature. As CO2 is evolved, stirring of the mixture at this temperature is continued for 18 hours. The mixture is subsequently cooled, the inorganic constituents are filtered off, and the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr). After removal of the excess α-bromopropionic acid methyl ester, the resulting yield is 990.3 g (79.6% of theory) of final product, which boils at 133°-134° (12 Torr). heated slowly stirring of the mixture at this temperature is continued for 18 hours The mixture is subsequently cooled the inorganic constituents are filtered off the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr) After removal of the excess α-bromopropionic acid methyl ester

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Furthermore, the reaction of 2,6-dimethylaniline at 120°-125° C., in the presence of sodium bicarbonate as an acid-binding agent, with a three-fold molar excess of methyl 2-bromopropionate has been disclosed in U.S. Pat. No. 4,008,066. With this process, N-(1'-methoxycarbonylethyl)-2,6-dimethylaniline is obtained in a yield of 79.6% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Furthermore, the reaction of 2,6-dimethylaniline at 120°-125° C., in the presence of sodium bicarbonate as an acid-binding agent, with a three-fold molar excess of methyl 2-bromopropionate has been disclosed in U.S. Pat. No. 4,008,066. With this process, N-(1'-methoxycarbonylethyl)-2,6-dimethylaniline is obtained in a yield of 79.6% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 990.3 g (= 4.76 g-moles) of α-(2,6-dimethylanilino)-propionic acid methyl ester is mixed with 605 g (= 5.7 g-moles) of sodium carbonate in 2.5 liters of benzene (absolute). An amount of 455 ml (= 5.7 g-moles) of monochloroacetyl chloride is then added dropwise and sufficiently slowly to ensure that a temperature of 30°-35° in the reaction mixture is not exceeded. After stirring has been maintained overnight at room temperature, the mixture is filtered off, and the filtrate concentrated in a rotary evaporator at ca. 50°. The resulting residue is recrystallised from ligroin (boiling range 65°-90° ). The yield obtained is 1132 g (= 83.8% of theory) of final product, M.P. 92°-94° (compound No. 3). to ensure that a temperature of 30°-35° in the reaction mixture the mixture is filtered off the filtrate concentrated in a rotary evaporator at ca. 50° The resulting residue is recrystallised from ligroin (boiling range 65°-90° ) The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g-moles of 2,6-dimethylaniline, 6.6 g-moles of NaHCO3 and 18.0 g-moles of α-bromopropionic acid methyl ester are placed together and heated slowly, with stirring, for 1 hour upto 120°-125° C. bath temperature. As CO2 is evolved, stirring of the mixture at this temperature is continued for 18 hours. The mixture is subsequently cooled, the inorganic constituents are filtered off, and the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr). After removal of the excess α-bromopropionic acid methyl ester, the resulting yield is 990.3 g (79.6% of theory) of final product, which boils at 133°-134° (12 Torr). heated slowly stirring of the mixture at this temperature is continued for 18 hours The mixture is subsequently cooled the inorganic constituents are filtered off the filtrate distilled in a water-jet vacuum (ca. 10- 12 Torr) After removal of the excess α-bromopropionic acid methyl ester

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Furthermore, the reaction of 2,6-dimethylaniline at 120° to 125° C., in the presence of sodium bicarbonate as an acid-binding agent, with a three-fold molar excess of methyl 2-bromopropionate has been disclosed in U.S. Pat. No. 4,008,066. With this process, N-(1'-methoxycarbonylethyl)-2,6-dimethylaniline is obtained in a yield of 79.6% of theory.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Furthermore, the reaction of 2,6-dimethylaniline at 120° to 125° C., in the presence of sodium bicarbonate as an acid-binding agent, with a three-fold molar excess of methyl 2-bromopropionate has been disclosed in U.S. Pat. No. 4,008,066. With this process, N-(1'-methoxycarbonylethyl)-2,6-dimethylaniline is obtained in a yield of 79.6% of theory.